Former Celtics Guard is a Big Reason Damian Lillard Chose Blazers Over Boston

The Boston Celtics traded Jrue Holiday back to the Portland Trail Blazers in exchange for guard Anfernee Simons. This move occurred two seasons after the Celtics initially acquired Holiday from Portland in September 2023. That initial acquisition saw Portland receive Malcolm Brogdon, Robert Williams, a 2024 first-round draft pick, and a 2029 unprotected first-round pick from Boston. Portland had only just obtained Holiday as part of the trade that sent Damian Lillard to the Milwaukee Bucks.

This new trade facilitates a reunion for Portland with Damian Lillard. Lillard, who spent his first eight NBA seasons with the Trail Blazers, was waived by the Milwaukee Bucks (who acquired him in 2023) to clear salary cap space. This allowed Lillard to return to Portland as a free agent, where he is set to sign a three-year contract. Lillard revealed that Holiday hinted at the reunion by sending him an eyeball emoji after Lillard was waived, knowing Lillard maintained strong ties to Portland.

Although Holiday and Lillard were involved in the same multi-team trade in 2023 and won an Olympic gold medal together for Team USA in 2020, they have never played on the same NBA team. Lillard is expected to miss the entire upcoming season recovering from a torn Achilles tendon sustained in the playoffs. Rumors suggest Holiday could potentially be traded again before Lillard returns. However, if Holiday remains with Portland, the duo will finally play together in the NBA when Lillard is healthy.